The 10 best holiday rentals in Simpson Bay, Sint Maarten | Booking.com
Skip to main content

Holiday Rentals in Simpson Bay

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Simpson Bay

The best holiday rentals in Simpson Bay

Check out our pick of great holiday rentals in Simpson Bay

Show hotels on map

Filter by:

Review score

Tradewinds Apartments Simpson Bay

Simpson Bay

Tradewinds Apartments Simpson Bay is set in Simpson Bay and features a pool with a view and sea views. There is a private entrance at the apartment for the convenience of those who stay.

A
Anne
From
Australia
Excellent location, great facilities, very welcoming staff
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 168 reviews
Price from
US$300
1 night, 2 adults
Check availability

The Hills Residence

Simpson Bay

Set in Simpson Bay, 600 metres from Kim Sha Beach, The Hills Residence offers accommodation with a rooftop pool, free private parking, a casino and a terrace.

A
Alexandre
From
Saint Barthelemy
We had an excellent stay in this tastefully decorated apartment close to all Simpson Bay attractions. The private garden and outdoor kitchen allowed us to concoct a delicious dinner with a view of the Simpson Bay lagoon. We will definitely come back to this apartment!
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 195 reviews
Price from
US$170.86
1 night, 2 adults
Check availability

Blue Dream Apartments

Simpson Bay

Boasting pool with a view, garden and views of pool, Blue Dream Apartments is set in Simpson Bay, 700 metres from Kim Sha Beach. A hot tub and a car rental service are available for guests.

J
Joanne
From
Antigua & Barbuda
Felt safe, host was very pleasant and welcoming, will do it all over again, very clean environment
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 725 reviews
Price from
US$99
1 night, 2 adults
Check availability

Villa Cleavage

Simpson Bay

Located in Simpson Bay and only 1.1 km from Kim Sha Beach, Villa Cleavage provides accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 16 reviews
Price from
US$115
1 night, 2 adults
Check availability

Mullet Bay Suites - Your Luxury Stay Awaits

Cupecoy (Near Simpson Bay)

Set in Cupecoy, Mullet Bay Suites - Your Luxury Stay Awaits offers beachfront accommodation 100 metres from Mullet Bay Beach and provides various facilities, such as pool with a view, a fitness centre...

S
Sofia
From
Estonia
The stay was absolutely amazing, very clean and new suite, perfect view from the balcony. The host was super attentive and responsive whenever we would have questions. Highly recommend to stay in these suites!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 159 reviews
Price from
US$226.80
1 night, 2 adults
Check availability

condostmaarten by the sea -Adults Only-

Koolbaai (Near Simpson Bay)

Condostmaarten by the sea -Adults Only- is situated in Koolbaai and has a pool with a view and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

a
aram
From
Afghanistan
Beautiful location. Always great waking up to the sounds of the ocean crashing against the rocks. the large swimming pool overlooking the sea is magical. the panoramic room is an amazing experience. great restaurant nearby. One thing I did learn is that you should definitely rent a car but everything is at 5minutes driving from the condo. Supermarkets, restaurants, beaches
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 126 reviews
Price from
US$403
1 night, 2 adults
Check availability

Modern 3BR Home with Own Private Pool

Philipsburg (Near Simpson Bay)

Boasting air-conditioned accommodation with a private pool, garden view and a patio, Modern 3BR Home with Own Private Pool is set in Philipsburg.

L
Luana
From
United Kingdom
Great location and the host was super helpful and responsive, suggesting things to do and asking how our first night was. The property was very modern and somewhere we could stay for a long trip.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 31 reviews
Price from
US$414.75
1 night, 2 adults
Check availability

1 bedroom apt with pool in Simpson Bay

Koolbaai (Near Simpson Bay)

Featuring air-conditioned accommodation with a private pool, 1 bedroom apt with pool in Simpson Bay is set in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

C
Claudia
From
United Kingdom
I liked the shared pool it was very nice.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 9 reviews
Price from
US$211.31
1 night, 2 adults
Check availability

Serenity Penthouse

Lowlands (Near Simpson Bay)

Set in Lowlands, Serenity Penthouse offers accommodation with rooftop pool, free WiFi and free private parking for guests who drive.

T
Tahfere
From
United States
The space was very clean , super spacious. Extremely relaxing ! Pool is heated view is amazing !
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
US$995
1 night, 2 adults
Check availability

The Castle

Philipsburg (Near Simpson Bay)

A recently renovated property, The Castle is set in Philipsburg near Great Bay Beach, Little Bay Beach.

N
Norbert
From
Germany
Englisch I would especially like to thank the owner Louis for his support. He made my extended stay even more pleasant than it already was. If I have to stay on Sint Maarten again, I will try to book there again.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 109 reviews
Price from
US$120
1 night, 2 adults
Check availability
All holiday rentals in Simpson Bay

Most booked holiday rentals in Simpson Bay and surroundings in the past month

See all

Enjoy breakfast in Simpson Bay and nearby

  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 159 reviews

    Set in Cupecoy, Mullet Bay Suites - Your Luxury Stay Awaits offers beachfront accommodation 100 metres from Mullet Bay Beach and provides various facilities, such as pool with a view, a fitness centre...

    From US$294.68 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 5 reviews

    Boasting air-conditioned accommodation with a private pool, Luxurious 1 bedroom Apt with pool in Simpson Bay is situated in Koolbaai. This property offers access to a terrace and free private parking.

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Boasting air-conditioned accommodation with a private pool, OASIS deluxe 1 bedroom apartment with Pool is situated in Koolbaai. The property has lake views and is 400 metres from Kim Sha Beach.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a balcony, OASIS Penthouse with private garden & shared pool is situated in Koolbaai.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 3 reviews

    Boasting air-conditioned accommodation with a private pool, The luxe 1 bedroom apartment is set in Koolbaai. This property offers access to a terrace and free private parking.

  • Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 2 reviews

    Located just 1.1 km from Simpson Bay Beach, Blue Sky 2 bedr apartment with pool in Simpson bay provides accommodation in Koolbaai with access to an outdoor swimming pool, a garden, as well as a lift.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Situated in Koolbaai, Blue Sky 1 bedroom apartment in Simpson Bay features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a private pool, Blue Sky apartment with lagoon view is located in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

Highly rated holiday rentals in Simpson Bay and nearby

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 9 reviews

    Featuring air-conditioned accommodation with a private pool, 1 bedroom apt with pool in Simpson Bay is set in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

    From US$205.41 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 121 reviews

    Diamond Gem Residence features rooms in Koolbaai. The property features sea and garden views. The guest house offers rooms with air conditioning, free private parking and free WiFi.

    From US$102.60 per night
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 31 reviews

    Boasting air-conditioned accommodation with a private pool, garden view and a patio, Modern 3BR Home with Own Private Pool is set in Philipsburg.

    From US$408.24 per night

  • The Black Palm

    Philipsburg
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 76 reviews

    The Black Palm is located in Philipsburg and features a private pool and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 19 reviews

    Boasting air-conditioned accommodation with a patio, Maho Beach House - Grand Ocean Suite is situated in Maho Reef. Private parking is available on site.

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 5 reviews

    Boasting air-conditioned accommodation with a patio, Patmay Greenery. Fresh air, vacation get away. Is set in Saint-James. This property offers access to a balcony, free private parking and free WiFi.

    From US$206.33 per night

  • Studio Blue Sunset

    Marigot
    8.0+ review score
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 99 reviews

    Featuring air-conditioned accommodation with a private pool, sea view and a terrace, Studio Blue Sunset is located in Marigot. This beachfront property offers access to a balcony and free WiFi.

  • Ti Koala

    Baie Nettle
    8.0+ review score
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 101 reviews

    Set 60 metres from Nettle Bay Beach, Ti Koala offers a private beach area, pool with a view and air-conditioned accommodation with a balcony and free WiFi.

    From US$179.59 per night

These holiday rentals in Simpson Bay and nearby have options with free cancellation

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 29 reviews

    Featuring air-conditioned accommodation with a balcony, Convenient Studio Apt Near Airport, Beaches & Food is located in Cupecoy. This apartment offers a garden.

    From US$133.27 per night

  • Fraicheur Des Caraibes

    Marigot
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 30 reviews

    Boasting sea views, Fraicheur Des Caraibes is situated in Marigot, around 300 metres from Baie de la Potence Beach. This beachfront property offers access to free WiFi and free private parking.

    From US$171.28 per night

  • Divine Rest

    Philipsburg
    Free cancellation options available
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 32 reviews

    Situated in Philipsburg, within 1.9 km of Little Bay Beach, Divine Rest offers accommodation with air conditioning.

  • The Castle

    Philipsburg
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 109 reviews

    A recently renovated property, The Castle is set in Philipsburg near Great Bay Beach, Little Bay Beach.

    From US$129.60 per night

  • Over The Hill Residence

    Grand Case
    Free cancellation options available
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 171 reviews

    Boasting a garden and barbecue facilities, Over The Hill Residence is situated in Grand Case. The property features sea and mountain views, and is 1.5 km from Grand Case Beach.

    From US$131.82 per night

  • Cozy apartment with garden in La Savane 75 m² mountain view is situated in Happy Bay and offers barbecue facilities.

    From US$355.69 per night

  • Charming Apartment in La Savane - 65 m² - Terrace with View is situated in Happy Bay.

    From US$349.88 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Situated in Happy Bay and only 1.5 km from Grand Case Beach, Charming Apartment in La Savane, 65 sqm with Terrace features accommodation with garden views, free WiFi and free private parking.

    From US$361.51 per night

Holiday Rentals with swimming pools in Simpson Bay and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 4 reviews

    Boasting garden views, Maho Beach House - Grand Ocean Suite - 2 Bedroom offers accommodation with a private beach area and a balcony, around 90 metres from Maho Beach.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Set in Upper Prince’s Quarter, this air-conditioned villa is located 7 km from Saint Martin. Amazing view of the Atlantic Ocean,and St. Barts from all rooms.

    From US$1,220 per night

  • Spacious villa with sea view in Saint Martin + private pool. Is located in Les Terres Basses and offers an outdoor swimming pool and a garden.

    From US$8,311.16 per night
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 6 reviews

    Located in Oyster Pond, 600 metres from Coralita Beach, The View, Pool, Sea View, Oyster Pond Balconies provides air-conditioned accommodation with a balcony and free WiFi.

    From US$233.04 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 54 reviews

    Located in Cul de Sac and only 1.9 km from Orient Bay Beach, C'RENITY VILLA provides accommodation with mountain views, free WiFi and free private parking.

    From US$296.41 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 47 reviews

    Boasting accommodation with a patio, C'Renity Studio is set in Cul de Sac.

    From US$174.36 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 21 reviews

    Boasting air-conditioned accommodation with a private pool, garden view and a patio, Spacious 3BR Home with Own Private Cozy Pool is situated in Koolbaai.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Featuring air-conditioned accommodation with a patio, Villa Casa Blue, between sky and ocean, Almond Grove is located in Koolbaai.

Holiday rentals that guests love in Simpson Bay

See all

Research, refine and make plans for your whole trip

Holiday Rentals on Sint Maarten

Eager to explore more of Sint Maarten? Find hotels up and down the country!

Holiday Rentals in Caribbean Islands

Extend your search and explore the surrounding area.

Holiday Rentals in St Martin

Extend your search and explore the surrounding area.

Flights to Simpson Bay

Find and compare prices for this popular flight route.

Holiday Rentals in Philipsburg

Discover another destination in Sint Maarten.

Holiday Rentals in Koolbaai

Discover another destination in Sint Maarten.

Hotels near Princess Juliana International Airport

Got a stopover, late arrival or early departure? Find hotels conveniently close to the airport.

Hotels near Robert L. Bradshaw International Airport

Perfect for a late arrival or early departure.

Holiday Rentals in Saint Martin

Find more hotels in a city close to Saint Martin.